Triethylamine → HCID 14459860, compound

HRID 1032703Notes

Reaction equation

HRID 1032703 reaction equation
Cl.Cl.[CH3:3][N:4]([CH3:11])[CH:5]1[CH2:10][CH2:9][CH2:8][NH:7][CH2:6]1.[NH:12]1[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[C:14]([C:21](O)=[O:22])=[N:13]1.C(N(CC)CC)C>ClCCl>[CH3:3][N:4]([CH3:11])[CH:5]1[CH2:10][CH2:9][CH2:8][N:7]([C:21]([C:14]2[C:15]3[C:20](=[CH:19][CH:18]=[CH:17][CH:16]=3)[NH:12][N:13]=2)=[O:22])[CH2:6]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 78250Indazole-3-carboxylic acidHCID 14459855N,N-Dimethylpiperidin-3-amine--hydrogen chloride (1/2)

Product 1

HCID 14459860HCID 14459860, compoundYield 12.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Dicyclohexycarbodiimide (1.25 g) was added to a stirred solution of 3-dimethylaminopiperidine dihydrochloride (1 g, 5 mmol), indazole3-carboxylic acid (1.05 g, 6 mmol) and triethylamine (1.25 g) in dichloromethane (25 ml). The mixture was stirred for 48 h, filtered and the filtrate extracted with 1M hydrochloric acid. The acid extracts were combined, washed with a little dichloromethane then basified with ammonia solution and back-extracted into chloroform. The extract was dried and evaporated. The residue was chromotographed on silica using methanol-methyl acetate (1:9) as eluent to give the product which was crystallised from a low volume of ethyl acetate to give the product (0.165 g) mp 141-142° C.

Workup

  1. filtrationfiltered
  2. extractionthe filtrate extracted with 1M hydrochloric acid
  3. washwashed with a little dichloromethane
  4. extractionback-extracted into chloroform
  5. customThe extract was dried
  6. customevaporated
  7. customto give the product which
  8. customwas crystallised from a low volume of ethyl acetate

Sources & evidence

ORD record
ord-6d67fd237c5e4ef3abcb4da9c38251ab
Source dataset
uspto-grants-1990_09
Patent number
US04959375

Reaction notes

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